'Black and White' (1999)

Theresa Dillion / Screen Gems

Tyson (center) appeared as himself in James Toback's 1999 film "Black and White," about white kids who become fascinated with Harlem's hip-hop culture. Although the film assembled talented actors and musicians Robert Downey Jr., Brooke Shields, Raekwon (left), Ghostface Killah, Oliver "Power" Grant (right) and more, it earned less than $6 million worldwide and was panned by critics. "It's also hard, excuse me, impossible, to watch 'Black and White' and not imagine that what you're watching are the voyeuristic indulgences of a middle-aged filmmaker playing out his most deep-seated and unresolved sexual fantasies and anxieties," reads a Los Angeles Times review of the film. "Easily the weirdest scene in a weirdly disjointed movie is one in which Tyson, playing himself, urges Harlem rapper Rich Bower (Power of Wu Tang Clan) to commit murder. You wonder if Tyson had his parole officer vet the script and doubt Toback ever thought to suggest it."

Tyson (center) appeared as himself in James Toback's 1999 film "Black and White," about white kids who become fascinated with Harlem's hip-hop culture. Although the film assembled talented actors and musicians Robert Downey Jr., Brooke Shields, Raekwon (left), Ghostface Killah, Oliver "Power" Grant (right) and more, it earned less than $6 million worldwide and was panned by critics. "It's also hard, excuse me, impossible, to watch 'Black and White' and not imagine that what you're watching are the voyeuristic indulgences of a middle-aged filmmaker playing out his most deep-seated and unresolved sexual fantasies and anxieties," reads a Los Angeles Times review of the film. "Easily the weirdest scene in a weirdly disjointed movie is one in which Tyson, playing himself, urges Harlem rapper Rich Bower (Power of Wu Tang Clan) to commit murder. You wonder if Tyson had his parole officer vet the script and doubt Toback ever thought to suggest it."